Water → 7-chloro-8-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2224255Notes

Reaction equation

HRID 2224255 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Cl:13][C:14]1[C:15]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:16]([NH:20][NH2:21])[N:17]=[N:18][CH:19]=1.O>C1COCC1>[Cl:13][C:14]1[CH:19]=[N:18][N:17]2[C:1](=[O:2])[NH:21][N:20]=[C:16]2[C:15]=1[C:22]1[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 597168331-(5-Chloro-4-(4-chlorophenyl)pyridazin-3-yl)hydrazine

Product 1

HCID 597168567-chloro-8-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,1′-carbonyldiimidazole (1.78 g, 11 mmol) in THF (10 mL) at RT was added a suspension of 1-(5-chloro-4-(4-chlorophenyl)pyridazin-3-yl)hydrazine (560 mg, 2.19 mmol) in THF (10 mL). After addition, the reaction became a clear solution and was stirred at RT for 1 h. The reaction mixture was then poured into water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. To the obtained residue was added EtOAc (20 mL), and the resulting yellow precipitate was collected by filtration and washed with hexane to give the title compound, 7-chloro-8-(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one as a yellow solid (300 mg, 61%). LC/MS (method A): RT=2.86 min, (M+H)+=281.

Workup

  1. additionAfter addition
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with saturated NaCl
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionTo the obtained residue was added EtOAc (20 mL)
  8. filtrationthe resulting yellow precipitate was collected by filtration
  9. washwashed with hexane

Sources & evidence

ORD record
ord-fa59e7618c314415a3633963e532abc6
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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